Dimethylamine → 4-((Dimethylamino)methyl)-4-methyloxazolidin-2-one

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Reaction Steps

A solution of 4-(chloromethyl)-4-methyloxazolidin-2-one (2.97 g, 19.9 mmol) in 2.0 M dimethylamine in THF (50 ml, 100 mmol) in a sealed tube was heated to 85° C. for 24 h, cooled to RT, and filtered through a coarse glass filter to remove precipitated dimethylammonium chloride. The filtrate was concentrated, and the residue purified by flash chromatography (3%→10% MeOH in CH2Cl2) to afford the oxazolidinone as a brown oil (1.02 g, 6.45 mmol, 32%), and the dihydrooxazole as a yellow oil (1.62 g, 10.2 mmol, 52%). Rf=0.5 in 10% MeOH in CH2Cl2. 1H NMR (CDCl3, 400 MHz) δ 1.35 (s, 3H), 2.33 (s, 6H), 2.37 (d, J=13.6 Hz, 1H), 2.43 (d, J=14.4 Hz, 1H), 4.02 (d, J=8.4 Hz, 1H), 4.18 (d, J=8.4 Hz, 1H), 5.2 (br s, 1H). ESI/APCI expected for C7H14N2O2: 158.11. Found: 159 (MH+).

Provenance & Evidence